Dimethylamine, hydrochloride → 2-{5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-N,N-dimethylacetamide

HRID 82105Notes

Reaction equation

HRID 82105 reaction equation
[K+].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]([C:21]3[C:29]4[CH:28]=[N:27][CH:26]=[N:25][C:24]=4[N:23]([CH2:30][C:31]([O-])=[O:32])[CH:22]=3)=[O:20])[CH:16]=[N:17][CH:18]=2)=[O:11])=[CH:5][CH:4]=1.Cl.[CH3:35][NH:36][CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1.C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]([C:21]3[C:29]4[CH:28]=[N:27][CH:26]=[N:25][C:24]=4[N:23]([CH2:30][C:31]([N:36]([CH3:37])[CH3:35])=[O:32])[CH:22]=3)=[O:20])[CH:16]=[N:17][CH:18]=2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70817542{5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid potassium salt

Product 1

HCID 708175352-{5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-N,N-dimethylacetamideYield 55%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

{5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid potassium salt (Example 307, 50 mg, 0.102 mmol) was added to a stirred solution of dimethyl amine HCl (12.5 mg, 0.153 mmol) and HATU (58.2 mg, 0.153 mmol) in pyridine (2 mL) and the resultant solution was stirred at 50° C. (reactivial) for 14 hours. The reaction was cooled to 25° C., diluted with DCM (5 mL) then quenched with saturated NaHCO3 (aq) (5 mL) and extracted with further DCM (3×5 mL). The organics were combined, washed with saturated brine (5 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by preparative HPLC gave the title compound in 55% yield, 26.6 mg.

Workup

  1. customthen quenched with saturated NaHCO3 (aq) (5 mL)
  2. extractionextracted with further DCM (3×5 mL)
  3. washwashed with saturated brine (5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-cb17e50213a641a9bf641795be74719b
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…